Chapter 9, Problem 59P

(a)

Interpretation Introduction

Interpretation:

The stereoisomeric products of (3S, 4S)-3-bromo-4-methylhexane in ${\text{S}}_{\text{N}}\text{2}$ reaction with methoxide base should be drawn.

Concept Introduction:

Primary alkyl halide undergoes ${\text{S}}_{\text{N}}{\text{2/E}}_{\text{2}}$ reaction: the substitution reaction is favored unless the nucleophile is sterically hindered.

Secondary alkyl halide undergoes ${\text{S}}_{\text{N}}{\text{2/E}}_{\text{2}}$ reaction: both the substitution and elimination products reaction are formed. Strong bases bulky bases and high temperature favors the elimination product.

(b)

Interpretation Introduction

Interpretation:

The stereoisomeric products of (3S, 4R)-3-bromo-4-methylhexane in ${\text{S}}_{\text{N}}\text{2}$ reaction with methoxide base should be drawn.

Concept Introduction:

Primary alkyl halide undergoes ${\text{S}}_{\text{N}}{\text{2/E}}_{\text{2}}$ reaction: the substitution reaction is favored unless the nucleophile is sterically hindered.

Secondary alkyl halide undergoes ${\text{S}}_{\text{N}}{\text{2/E}}_{\text{2}}$ reaction: both the substitution and elimination products reaction are formed. Strong bases bulky bases and high temperature favors the elimination product.

(c)

Interpretation Introduction

Interpretation:

The stereoisomeric products of (3R, 4R)-3-bromo-4-methylhexane in ${\text{S}}_{\text{N}}\text{2}$ reaction with methoxide base should be drawn.

Concept Introduction:

Primary alkyl halide undergoes ${\text{S}}_{\text{N}}{\text{2/E}}_{\text{2}}$ reaction: the substitution reaction is favored unless the nucleophile is sterically hindered.

Secondary alkyl halide undergoes ${\text{S}}_{\text{N}}{\text{2/E}}_{\text{2}}$ reaction: both the substitution and elimination products reaction are formed. Strong bases bulky bases and high temperature favors the elimination product.

(d)

Interpretation Introduction

Interpretation:

The stereoisomeric products of (3R, 4S)-3-bromo-4-methylhexane in ${\text{S}}_{\text{N}}\text{2}$ reaction with methoxide base should be drawn.

Concept Introduction:

Primary alkyl halide undergoes ${\text{S}}_{\text{N}}{\text{2/E}}_{\text{2}}$ reaction: the substitution reaction is favored unless the nucleophile is sterically hindered.

Secondary alkyl halide undergoes ${\text{S}}_{\text{N}}{\text{2/E}}_{\text{2}}$ reaction: both the substitution and elimination products reaction are formed. Strong bases bulky bases and high temperature favors the elimination product.